Isolation and Characterization of Antibacterial Carotane Sesquiterpenes from Artemisia argyi Associated Endophytic Trichoderma virens QA-8
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structural Elucidation of the New Compounds
2.2. Antibacterial Activities of the Isolated Compounds
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Plant and Fungal Materials
3.3. Fermentation, Extraction and Isolation
3.4. Spectroscopic Data
3.5. X-Ray Crystallographic Analysis of Compounds 1–3, 5, 9, and 10
3.6. Antibacterial Assays
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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No. | 1 | 2 | 3 | 4 | 5 |
---|---|---|---|---|---|
2 | 3.09, d (7.0) | 1.41, m (overlap) | 1.50, m | 1.64, m (overlap) | 1.49, m (overlap) |
3 | 3.63, d (7.0) | 3.88, m | 3.88, dd (7.2, 1.6) | 3.87, m | 3.88, t (4.4) |
5 | 1.26, dd (11.4, 1.7) | 1.41, m (overlap) | 1.66, m | 1.64, m (overlap) | 1.36, m |
6α | 1.49, m | 1.56, m | 1.78, m | 5.80, d (11.2) | 1.30, m |
6β | 1.37, m | 1.49, m | 1.78, m | 1.49, m (overlap) | |
7α | 2.00, m (overlap) | 4.03, m | 1.43, m | 5.39, d (11.2) | 1.81, m (overlap) |
7β | 2.00, m (overlap) | 1.43, m | 2.11, dd (14.9, 3.2) | ||
8 | 2.38, m | ||||
9 | 5.32, br d (7.0) | 5.26, m | 5.57, m | 5.50, br d (8.2) | |
10α | 1.59, dd (14.4, 1.2) | 1.87, dd (14.0, 9.1) | 2.43, d (14.4) | 2.18, m | 1.81, m (overlap) |
10β | 2.07, dd (14.4, 8.9) | 1.68, m | 2.30, d (14.4) | 2.18, m | 1.99, dd (14.4, 8.9) |
11 | 1.66, m | 1.74, m | 1.70, m | 1.64, m (overlap) | 1.69, m |
12 | 0.79, d (6.9) | 0.81, d (6.9) | 0.79, d (6.9) | 0.85, d (6.9) | 0.81, d (6.9) |
13 | 0.85, d (6.7) | 0.88, d (6.9) | 0.86, d (6.7) | 0.78, d (6.9) | 0.87, d (6.7) |
14 | 1.70, s | 1.71, s | 0.96, d (6.9) | 1.74, s | 3.76, s |
15 | 0.71, s | 0.88, s | 1.06, s | 0.98, s | 0.92, s |
2-OH | 4.16, s | ||||
3-OH | 5.39, s | 5.21, d (4.2) | 5.35, s | ||
4-OH | 3.53, s | 3.69, s | 3.76, s | 3.60, br s | |
7-OH | 4.66, d (5.1) |
No. | 1 | 2 | 3 | 4 | 5 |
---|---|---|---|---|---|
1 | 44.5, C | 40.7, C | 40.2, C | 44.6, C | 41.6, C |
2 | 78.4, CH | 49.6, CH2 | 50.3, CH2 | 47.9, CH2 | 50.0, CH2 |
3 | 70.6, CH | 70.1, CH | 70.4, CH | 71.8, CH | 70.4, CH |
4 | 79.0, C | 82.5, C | 82.1, C | 82.1, C | 82.6, C |
5 | 54.3, CH | 53.5, CH | 55.4, CH | 47.2, CH | 57.7, CH |
6 | 20.2, CH2 | 31.7, CH2 | 18.4, CH2 | 143.8, CH | 21.1, CH2 |
7 | 34.1, CH2 | 72.6, CH | 33.0, CH2 | 125.3, CH | 30.0, CH2 |
8 | 138.4, C | 143.6, C | 46.3, CH | 129.0, C | 142.6, C |
9 | 122.3, CH | 119.6, CH | 214.3, C | 127.4, CH | 121.4, CH |
10 | 40.0, CH2 | 41.5, CH2 | 57.3, CH2 | 27.0, CH2 | 42.1, CH2 |
11 | 34.8, CH | 34.4, CH | 34.7, CH | 35.0, CH | 34.7, CH |
12 | 17.6, CH3 | 17.7, CH3 | 17.6, CH3 | 17.7, CH3 | 17.7, CH3 |
13 | 17.1, CH3 | 17.2, CH3 | 17.1, CH3 | 17.3, CH3 | 17.1, CH3 |
14 | 27.1, CH3 | 21.1, CH3 | 22.8, CH3 | 26.9, CH3 | 66.9, CH2 |
15 | 13.9, CH3 | 20.9, CH3 | 23.2, CH3 | 21.4, CH3 | 20.9, CH3 |
No. | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | Chloramphenicol |
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
EC | 16 | 32 | 0.5 | 0.5 | 0.5 | 16 | 16 | 0.5 | 16 | 16 | 0.5 | 8 | 0.5 |
ML | – | 32 | – | – | 8 | 4 | 0.5 | 2 | – | – | 32 | 8 | 1 |
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Shi, X.-S.; Song, Y.-P.; Meng, L.-H.; Yang, S.-Q.; Wang, D.-J.; Zhou, X.-W.; Ji, N.-Y.; Wang, B.-G.; Li, X.-M. Isolation and Characterization of Antibacterial Carotane Sesquiterpenes from Artemisia argyi Associated Endophytic Trichoderma virens QA-8. Antibiotics 2021, 10, 213. https://doi.org/10.3390/antibiotics10020213
Shi X-S, Song Y-P, Meng L-H, Yang S-Q, Wang D-J, Zhou X-W, Ji N-Y, Wang B-G, Li X-M. Isolation and Characterization of Antibacterial Carotane Sesquiterpenes from Artemisia argyi Associated Endophytic Trichoderma virens QA-8. Antibiotics. 2021; 10(2):213. https://doi.org/10.3390/antibiotics10020213
Chicago/Turabian StyleShi, Xiao-Shan, Yin-Ping Song, Ling-Hong Meng, Sui-Qun Yang, Dun-Jia Wang, Xing-Wang Zhou, Nai-Yun Ji, Bin-Gui Wang, and Xiao-Ming Li. 2021. "Isolation and Characterization of Antibacterial Carotane Sesquiterpenes from Artemisia argyi Associated Endophytic Trichoderma virens QA-8" Antibiotics 10, no. 2: 213. https://doi.org/10.3390/antibiotics10020213